CN107406696A - 新颖的电沉积体系 - Google Patents
新颖的电沉积体系 Download PDFInfo
- Publication number
- CN107406696A CN107406696A CN201680009532.9A CN201680009532A CN107406696A CN 107406696 A CN107406696 A CN 107406696A CN 201680009532 A CN201680009532 A CN 201680009532A CN 107406696 A CN107406696 A CN 107406696A
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- China
- Prior art keywords
- bismuth
- composition
- inorganic
- containing compound
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000004070 electrodeposition Methods 0.000 title claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 110
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 73
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000000576 coating method Methods 0.000 claims abstract description 50
- 239000011248 coating agent Substances 0.000 claims abstract description 46
- 230000007797 corrosion Effects 0.000 claims abstract description 23
- 238000005260 corrosion Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims description 68
- 239000000463 material Substances 0.000 claims description 45
- 229920005989 resin Polymers 0.000 claims description 34
- 239000011347 resin Substances 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 33
- -1 oxygen anion Chemical class 0.000 claims description 25
- 239000000049 pigment Substances 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 17
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000839 emulsion Substances 0.000 claims description 13
- 229940104825 bismuth aluminate Drugs 0.000 claims description 12
- 238000001962 electrophoresis Methods 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 150000001621 bismuth Chemical class 0.000 claims description 10
- PDSAKIXGSONUIX-UHFFFAOYSA-N hexaaluminum;dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Bi+3].[Bi+3] PDSAKIXGSONUIX-UHFFFAOYSA-N 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 239000008199 coating composition Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 6
- SKKNACBBJGLYJD-UHFFFAOYSA-N bismuth magnesium Chemical compound [Mg].[Bi] SKKNACBBJGLYJD-UHFFFAOYSA-N 0.000 claims description 5
- SFOQXWSZZPWNCL-UHFFFAOYSA-K bismuth;phosphate Chemical compound [Bi+3].[O-]P([O-])([O-])=O SFOQXWSZZPWNCL-UHFFFAOYSA-K 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- QYIGOGBGVKONDY-UHFFFAOYSA-N 1-(2-bromo-5-chlorophenyl)-3-methylpyrazole Chemical compound N1=C(C)C=CN1C1=CC(Cl)=CC=C1Br QYIGOGBGVKONDY-UHFFFAOYSA-N 0.000 claims description 4
- KKMOSYLWYLMHAL-UHFFFAOYSA-N 2-bromo-6-nitroaniline Chemical compound NC1=C(Br)C=CC=C1[N+]([O-])=O KKMOSYLWYLMHAL-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- YISOXLVRWFDIKD-UHFFFAOYSA-N bismuth;borate Chemical compound [Bi+3].[O-]B([O-])[O-] YISOXLVRWFDIKD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 229910000831 Steel Inorganic materials 0.000 claims description 3
- 239000010959 steel Substances 0.000 claims description 3
- 229910000014 Bismuth subcarbonate Inorganic materials 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- RHGQOMYDGHIKFH-GNOQXXQHSA-K bis[[(z)-octadec-9-enoyl]oxy]bismuthanyl (z)-octadec-9-enoate Chemical compound [Bi+3].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O RHGQOMYDGHIKFH-GNOQXXQHSA-K 0.000 claims description 2
- MGLUJXPJRXTKJM-UHFFFAOYSA-L bismuth subcarbonate Chemical compound O=[Bi]OC(=O)O[Bi]=O MGLUJXPJRXTKJM-UHFFFAOYSA-L 0.000 claims description 2
- 229940036358 bismuth subcarbonate Drugs 0.000 claims description 2
- 229960004645 bismuth subcitrate Drugs 0.000 claims description 2
- ZQUAVILLCXTKTF-UHFFFAOYSA-H bismuth;tripotassium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].[K+].[K+].[Bi+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZQUAVILLCXTKTF-UHFFFAOYSA-H 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- IZRTVYMPRPTBAI-UHFFFAOYSA-K dibenzoyloxybismuthanyl benzoate Chemical compound [Bi+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 IZRTVYMPRPTBAI-UHFFFAOYSA-K 0.000 claims description 2
- FIMTUWGINXDGCK-UHFFFAOYSA-H dibismuth;oxalate Chemical compound [Bi+3].[Bi+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O FIMTUWGINXDGCK-UHFFFAOYSA-H 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 2
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims description 2
- IWUXOURWOCRGST-UHFFFAOYSA-N C(N)(S)=S.[Bi] Chemical compound C(N)(S)=S.[Bi] IWUXOURWOCRGST-UHFFFAOYSA-N 0.000 claims 1
- 241000219000 Populus Species 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- ZREIPSZUJIFJNP-UHFFFAOYSA-K bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 claims 1
- 229960000782 bismuth subsalicylate Drugs 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000005096 rolling process Methods 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 238000004132 cross linking Methods 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 239000011342 resin composition Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 230000008569 process Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 9
- 238000007711 solidification Methods 0.000 description 9
- 230000008023 solidification Effects 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 4
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 229940049676 bismuth hydroxide Drugs 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- DQUIAMCJEJUUJC-UHFFFAOYSA-N dibismuth;dioxido(oxo)silane Chemical compound [Bi+3].[Bi+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O DQUIAMCJEJUUJC-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000006254 rheological additive Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009974 thixotropic effect Effects 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 241000557626 Corvus corax Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005955 Ferric phosphate Substances 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940032958 ferric phosphate Drugs 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 2
- 229910000399 iron(III) phosphate Inorganic materials 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ZUAURMBNZUCEAF-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethanol Chemical compound OCCOCCOC1=CC=CC=C1 ZUAURMBNZUCEAF-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- TUJDZBCXUPOERQ-UHFFFAOYSA-N 3-ethylpentylhydrazine Chemical class CCC(CC)CCNN TUJDZBCXUPOERQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
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Abstract
描述了用于电沉积的电泳涂布体系。该体系包含无机含铋化合物或无机含铋化合物与有机含铋化合物的混合物。该体系展示出高度交联，并产生了具有最佳交联和耐腐蚀性的固化涂层。
Description
相关申请的交叉引用
本申请要求2015年2月10日提交的题为“用于阴极电泳涂布体系的催化剂(Catalyst For Cathodic Electrocoat System)”的美国临时申请No.62/114,228的优先权，其全部内容通过引用并入本文。
发明背景
通常将涂料涂覆到基材上以提供保护性和/或装饰性品质。特别地，经常将涂料涂覆到金属表面上以抑制或防止腐蚀。
用于涂覆涂料的一种有效技术包括电泳涂布工艺，其通常包括利用施加的电势使组合物沉积到导电基材上。电泳涂布是很流行的，这是因为与其他涂布工艺相比，其能够提供改进的腐蚀防护和低环境污染。
电泳涂布方法是本领域公知的。商业电泳涂布工艺有时使用阴离子电泳涂布工艺，其中被涂布的基材充当阳极。然而，阴极或阳离子电泳涂布工艺倾向于提供具有优异耐腐蚀性的涂层，现今是最普遍的电泳涂布方法。例如，绝大多数汽车底漆涂料现在通过阳离子电沉积来生产。
高度交联的涂层对于耐腐蚀性以及美学吸引力而言是期望的。通常，这样的涂层通过可交联官能团和封闭异氰酸酯基团之间的反应形成。催化剂通常用于促进交联反应。
各种催化剂是本领域已知的。有机锡化合物，例如二丁基氧化锡(DBTO)、二辛基氧化锡(DOTO)、二月桂酸二丁基锡(DBTDL)是用于电泳涂布中的已知催化剂。这些商业催化剂中最常用的是DBTO，其是可以容易地掺入电泳涂布组合物中的固体材料。然而，与锡化合物相关的人类健康风险和环境问题越来越受到重视。有机锡化合物(包括DBTO)有时被认为是污染物，并且存在增加的监管压力以显著减少或消除这种化合物的使用。因此，在电泳涂布体系中，正在寻求有机锡化合物(特别是二丁基锡化合物诸如DBTO)的替代物。
多种非有机锡催化剂可用于电泳涂布体系中，但并非所有这类催化剂都与DBTO一样有效。已经提出某些含铋化合物作为有机锡催化剂的替代物。例如，羧酸的有机铋盐已经被描述为电沉积催化剂。然而，这些化合物是液态的、疏水的且不混溶于水。因此，它们不能容易地掺入电泳涂布浴的颜料糊中并且倾向于渗出到表面，从而在电泳涂布浴中产生不期望的漂浮物。
已经提出了各种其它含铋化合物作为电泳涂布工艺的催化剂。包括例如金属铋、三氧化铋、有机硫基铋化合物等，它们通常与其它催化化合物(如金属锆、有机锡化合物或杂环化合物如巯基官能化合物)一起使用。
由上述可以理解，本领域需要的是用于电沉积的有效催化剂，其基本上或者甚至完全不含有机锡化合物，但是能够容易地掺入电泳涂布浴中而不引起不期望的漂浮问题或损失期望的固化膜性质例如耐腐蚀性。本文公开了并要求保护这种催化剂、含有这种催化剂的组合物以及制备和使用催化剂和组合物的方法。
概述
本说明书提供了使用不含有机锡的固化催化剂进行电沉积的组合物和方法。由本文所述的电沉积组合物形成的优选涂层提供最佳的交联和性能特征，包括增强的耐腐蚀性。
在一个实施方式中，本说明书提供了包含无机含铋化合物的可电沉积组合物。
在另一个实施方式中，本说明书提供了用于电沉积的组合物，其包含电沉积树脂组分、任选的交联组分、任选的羧酸组分和无机含铋化合物。
在另一个实施方式中，本说明书提供了方法，所述方法包括以下步骤：将包含至少一种可交联官能团的电沉积树脂组分与封闭异氰酸酯组分、脂族羧酸组分和至少无机含铋化合物组合。
在另一个实施方式中，本说明书提供了使用固化催化剂的方法。该方法包括以下步骤：提供包含无机含铋化合物作为固化催化剂的组合物，并向使用者提供将所述包含固化催化剂的组合物加入电沉积浴中的指示。
在另一个实施方式中，本说明书提供了用于在基材上电沉积涂料的方法。该方法包括以下步骤：提供包含电沉积树脂组分和多异氰酸酯组分的乳液以及包含无机含铋化合物的颜料糊。该方法还包括将乳液与颜料糊混合以提供电沉积浴的步骤和阴极电泳涂布给定基材的步骤。
本发明的上述概述并非意图描述本发明的每一个公开的实施方式或每一种实施情况。下面的描述更具体地举例说明说明性的实施方式。在整个申请的几个地方，通过实例的列表提供指导，这些实例可以以各种组合方式使用。在每种情况中，所列举的列表仅用作代表性的组，而不应该被解释为穷举性的列表。
在如下的附图和说明中阐明了本发明的一个或多个实施方式的细节。从说明书和附图以及权利要求出发，本发明的其它特征、目的和优点是明显的。
选择的定义
除另有指明外，本文中使用的下列术语具有下面提供的含义。
术语“组分”指的是包含具体特征或结构的任意化合物。组分的实例包括化合物、单体、寡聚物、聚合物以及其中包含的有机基团。
术语“交联剂”是指能够在聚合物之间或者在同一聚合物的不同区域之间形成共价链接的分子。该术语与“交联组分”可互换使用。
在可分散性聚合物这样的上下文中使用时，术语“分散体”是指可分散性聚合物和载体的混合物。术语“分散体”意欲涵盖术语“溶液”。
术语“含锡化合物”在本文中用作对各种锡化合物的提及，包括有机锡化合物例如二丁基氧化锡，例如目前受监管关注、限制或禁止的那些。“不含锡”或“不含标记”在本文中用于表示不含这些化合物的化合物，但锡仍可以其它形式存在。
当在涂料涂覆在表面或基材之上的上下文中使用时，术语“在…之上”既包括涂料直接涂覆于表面或基材上，也包括涂料间接涂覆于表面或基材上。因此，例如，涂覆在覆盖基材的底漆层上的涂层构成涂覆在基材上的涂层。
在本文中使用时，术语“电沉积”是指使用电流来减少溶解的金属离子以在充当电极的金属基材上形成涂层的方法。当基材形成阴极时，该方法被称为阴极电沉积。当基材形成阳极时，该方法被称为阳极电沉积。术语“电泳涂布”与“电沉积”在本文中可互换使用，并且可用于电泳涂布的组合物或组分被视为“可电沉积的”。
在本文中使用时，术语“催化效果”或“催化有效的”是指涂料组合物中的组分促进组合物有效交联的能力。在这种上下文中，当发生固化反应时，存在催化效果。相对于对照催化剂，更好的催化剂提供更快的固化或在更低的固化温度下固化或两者。
在本文中使用时，术语“基本上不溶”是指在电沉积浴的正常pH和温度条件下，不超过约1重量％的组分溶解在水中。在本文中使用时，“通常不溶”是指不超过0.2重量％的组分溶解，而术语“完全不溶”是指在电沉积浴的正常pH和温度条件下，不超过0.1重量％的组分溶解在水中。
除另有指明外，术语“聚合物”包括均聚物和共聚物(即两种或更多种不同单体的聚合物)二者。
当在说明书和权利要求中出现时，术语“包含”、“包括”及其变体并不具有限制性意义。
在本文中使用时，术语“提供”旨在广义地包括可得、供应或获得组分、基材、部件等。该术语可包括制造，以及通过购买获得，通过销售供应，或组分、基材、零件的其他类型的转移等。
术语“优选的”和“优选地”指的是在某些情况下可以提供某些优点的本发明的实施方式。但是，在相同情况或其他情况下，其他实施方式也可以是优选的。此外，一个或多个优选的实施方式的表述并不意味着其他实施方式不可用，并且并非意图将其他实施例排除在本发明的范围外。
当在本文中使用时，不使用数量词、“至少一个”、和“一个或多个”可互换使用。因此，例如，包含添加剂的涂料组合物可被解释为表示该涂料组合物包含“一种或多种”添加剂。
同样在本文中，以端点描述的数值范围包括该范围内所包含的所有数值(例如1至5包括1、1.5、2、2.75、3、3.80、4、5等)。此外，范围的公开包括在较宽范围内包含的所有子集(例如1至5公开了1至4、1.5至4.5、1至2等)的公开。
详细说明
本说明书提供了包含无机含铋化合物的可电沉积组合物。所述组合物可用于任何类型的电泳涂布方法，包括阳极方法和阴极方法。
本说明书提供了用于电沉积的组合物和方法。所述组合物优选包含电沉积树脂组分、任选的多异氰酸酯组分、任选的酸官能组分和至少无机含铋化合物。本文所述的方法优选包括将包含电沉积树脂组分的乳液与通常且优选以颜料糊形式提供的无机含铋化合物以及任何任选的多异氰酸酯和酸组分组合在一起。所述方法优选还包括将乳液与颜料糊混合以提供电沉积浴的步骤和电泳涂布给定基材的步骤。
在一个实施方式中，本说明书提供了用于电沉积的组合物。所述组合物包含可电沉积的树脂组分。在一方面，所述树脂组分是具有自交联官能团或可交联官能团的树脂。例如，树脂组分可以具有羟基、异氰酸酯、胺、环氧、丙烯酸酯、乙烯基、硅烷、氨基甲酸酯、乙酰乙酸酯官能团或这些官能团的任何合适的组合等。在优选的方面，树脂具有可阳离子化的官能团，例如伯胺、仲胺或叔胺官能团。
电泳涂布方法是本领域公知的，至少以下专利中描述了该方法的各个方面：3,582,481；3,761,371；3,793,278；3,922,253；3,959,106；3,962,165；3,975,346；3,990,953；4,001,101；4,017,438；4,031,050；4,064,028；4,101,486；4,180,442；4,192,720；4,383,073；4,388,435；4,416,752；4,419,467；4,432,850；4,789,566；4,559,393；4,854,366；4,879,325；4,978,728；5,0794,979；5,116,472；5,152,880；5,338,434；5,582,704；5,670,441；6,013,167；6,033,545；6,207,731；6,547,952；6,662,588；6,123,822；6,353,057；6,517,695；8,137,804；8,152,983等。
树脂组分可以是阳极组分或阴极组分。当涂覆涂料用于装饰目的时，通常使用阳极组分，而阴极组分通常在需要最佳耐腐蚀性时使用。在优选的方面，树脂组分是阴极组分。
在一方面，树脂组分具有聚合物骨架。用于聚合物骨架的合适聚合物包括但不限于环氧树脂、丙烯酸类、聚烯烃、聚氨酯、多胺、醇酸树脂、聚酯等。环氧树脂和丙烯酸树脂目前是优选的。
在一方面，树脂组分是丙烯酸树脂、苯乙烯改性的丙烯酸树脂或丙烯酸杂合树脂，更优选阴极丙烯酸体系。任何以前公开的用于阴极电泳涂布组合物中的丙烯酸树脂体系均可以在本文中使用。美国专利Nos.3,582,481；3,761,371；3,990,953；4,180,442；4,192,720；4,416,752；4,854,366；5,116,472；5,152,880；6,013,167；6,033,545；6,207,731；6,547,952和6,662,588中进一步描述了这种类型的体系。用于本发明的合适商业阴极丙烯酸类包括但不限于POWERCRON(PPG)、ELECTROCLEAR(PPG)、V-SHIELD(Valspar)、VECTROGARD700、(Valspar)和ACRONAL(BASF)系列产品中使用的树脂。
在一个优选的方面，树脂组分是环氧树脂，更优选胺官能环氧树脂或胺化环氧树脂，甚至更优选阴极环氧体系。任何以前公开的用于阴极电泳涂布组合物中的胺官能环氧树脂均可以在本文中使用。例如，美国专利No.4,031,050描述了电沉积树脂，其是环氧基树脂和伯胺或仲胺的反应产物。美国专利No.4,017,438描述了环氧基树脂和封闭伯胺的反应产物。美国专利Nos.3,962,165；3,975,346；4,001,101和4,101,486公开了阳离子电沉积树脂，其是环氧基树脂和叔胺的反应产物。美国专利Nos.3,959,106和3,793,278描述了阳离子电沉积树脂，其是具有锍盐基团的环氧基树脂；美国专利No.4,383,073描述了阳离子电沉积树脂，其是具有氨基甲酰基吡啶鎓盐基团的环氧基树脂。美国专利No.4,419,467公开了与伯胺、仲胺和叔胺基团以及季铵基团和三元锍基团反应的环氧基树脂。
用于本发明的市售阴极环氧体系包括但不限于POWERCRON(PPG)、FRAMECOAT(PPG)、VECTROGARD 900和VECTROGARD 950(Valspar)、AQUA EC 2000和AQUA EC 3000(Axalta)以及CATHOGUARD系列产品(BASF)中使用的树脂。
在一个实施方式中，基于电沉积组合物中树脂固体的总重量，树脂组分的存在量为约40-95重量％，优选约55-80重量％，更优选约60-70重量％。
在一个方面，树脂组分是自交联的；在另一个方面，树脂组分可与任选的交联剂交联，所述交联剂能够与树脂组分的官能团反应。
用于本文所述组合物和方法中的合适的任选交联剂包括例如氨基塑料树脂、多异氰酸酯、聚环氧化物、多元酸和多胺、其组合或混合物等。
在一个优选的方面，交联剂是多异氰酸酯。合适的多异氰酸酯的实例包括但不限于芳族、脂环族或脂族多异氰酸酯化合物，优选二异氰酸酯化合物例如甲苯二异氰酸酯(TDI)、亚二甲苯基二异氰酸酯(XDI)、甲苯亚二甲苯基二异氰酸酯(TMXDI)、亚苯基二异氰酸酯、四亚甲基二异氰酸酯、六亚甲基二异氰酸酯(HMDI)、亚甲基二异氰酸酯、亚甲基二苯基二异氰酸酯(MDI)、异佛尔酮二异氰酸酯(IPDI)、异氰酸酯预聚物、其组合或混合物等。在一个优选的方面，用作本文所述树脂组分的交联剂的多异氰酸酯是亚甲基二苯基二异氰酸酯(MDI)。这种交联剂是本领域公知的，并且在许多专利中有描述，包括例如美国专利Nos.3,894,922；3,947,339；3,984,299；3,959,106；4,017,438；4,038,232；4,031,050，4,101,486；4,134,816；4,176,221；4,182,831；4,182,833；4,225,478；4,225,479；4,260,697；4,297,255；4,310,646；4,393,179；4,339,369；4,452,681；4,452,930和4,452,963。
本文所用的优选多异氰酸酯交联剂包括封闭多异氰酸酯。合适的封闭剂包括例如(a)内酰胺化合物，例如ε-己内酰胺、γ-己内酰胺等；(b)肟化合物，例如甲基乙基酮肟等；(c)酚类，例如苯酚、对-叔丁基苯酚、甲酚等；(d)脂族醇，例如丁醇、2-乙基己醇等；(e)含有活性氢基团的化合物，包括芳族醇例如苯基卡必醇、甲基苯基卡必醇等，二烷基化合物例如丙二酸二乙酯、二甲基吡唑等；和(f)醚醇等。在一个优选的方面，用醇封闭本文所用的多异氰酸酯交联剂。
在一个实施方式中，其中树脂组分是自交联的，不需要另外的交联剂，但仍可使用一种或多种交联剂。在另一个实施方式中，基于电沉积组合物中树脂固体的总重量，交联剂的存在量为约10-60重量％，优选20-45重量％，更优选30-40重量％。
阴极电沉积中使用的组合物通常通过包含酸组分而被中和。因此，在一个实施方式中，本文所述的电沉积组合物包含任选的酸组分，例如无机或有机的酸组分。已知适合与电沉积体系一起使用的任何酸组分均可以在本文中使用，但目前优选羧酸官能化合物。合适的羧酸官能化合物包括例如(i)芳族酸，包括苯甲酸、水杨酸及其混合物或组合等；(ii)脂族酸，包括甲酸、乙酸等；(iii)α-羟基酸，例如乳酸、乙醇酸、柠檬酸及其混合物或组合等。例如，美国专利No.6,190,524中描述了合适的酸的实例。在一个优选的方面，羧酸官能组分是乳酸。
在一个实施方式中，任选的羧酸官能组分以足以中和树脂并提供稳定乳液的量存在。在一方面，酸官能组分优选以与树脂中的可中和官能团的摩尔比为1∶1、更优选为0.5∶1、更优选为0.3∶1而存在。
本文所述的电沉积组合物还包含不含有机锡的固化催化剂。不限于理论，在一些实施方式中，人们认为催化剂可以帮助封闭多异氰酸酯解封，以在固化过程期间(例如，加热或烘烤至约176℃的温度)与树脂组分的聚合物骨架上的可交联官能团交联。
在一个实施方式中，用于本文所述组合物和方法中的合适的不含有机锡的催化剂优选包括无机含铋化合物，优选各种阴离子的多价铋盐，更优选金属氧阴离子的铋盐。这些化合物包括其无水形式，以及各种水合物，包括半水合物、五水合物和其它水合形式，及其混合物和组合等。
出乎意料地，无机含铋化合物展示出最佳的分散性和催化活性。此外，与常规使用的羧酸铋不同，本文所述的无机铋化合物优选在电沉积过程期间不渗出或漂浮到浴的表面。
各种阴离子的这种铋盐的合适实例包括但不限于硅酸铋、硅铝酸铋镁、铝酸铋、硼酸铋、锰酸铋、磷酸铋等。虽然氢氧化铋和三氧化铋可以为电沉积组合物提供耐腐蚀性益处，但目前预期自身不能提供催化效果。
在一个优选的方面，无机含铋化合物是金属氧阴离子的铋盐，例如铝酸铋、锰酸铋及其混合物或组合等。
在一个实施方式中，合适的不含有机锡的催化剂优选包括在室温(25℃)下为固体的无机含铋化合物。固态无机含铋化合物的实例包括但不限于硅酸铋、铝硅酸铋镁、铝酸铋、硼酸铋、锰酸铋、磷酸铋及其水合物等。
在一个实施方式中，合适的不含有机锡的催化剂优选包括在阴极电沉积浴的正常操作pH(即约4-6的pH)下和阴极电沉积浴的正常操作温度(即约37℃)下基本上不溶于水、更优选通常不溶或完全不溶于水的无机含铋化合物。不溶性无机含铋化合物的实例包括但不限于铝酸铋、硅酸铋、铝硅酸铋镁、硼酸铋、锰酸铋、磷酸铋及其混合物或组合。
在一个实施方式中，合适的不含有机锡的催化剂优选包括在阴极电沉积浴的正常操作pH和温度下为白色或无色的无机含铋化合物。白色或无色无机含铋化合物的实例包括但不限于铝硅酸铋镁、铝酸铋、氢氧化铋、硼酸铋、磷酸铋等。
在一个优选的实施方式中，无机含铋化合物是铝酸铋，更优选铝酸铋水合物，其可以从各种来源(包括例如Sigma-Aldrich)商购获得。应当注意，金属氧阴离子的铋盐(诸如铝酸铋和铝酸铋水合物)可以与少量的其它无机含铋化合物(包括例如三氧化铋和氢氧化铋)缔合(associate)，或者被部分转化为少量的其它无机含铋化合物(包括例如三氧化铋和氢氧化铋)。虽然这些物质可以为电沉积组合物提供耐腐蚀性益处，但目前预期自身不能提供催化效果。
在一些实施方式中，无机含铋化合物可以与一种或多种有机含铋化合物组合使用，目前认为以前公开的用于阴极电泳涂布组合物中的有机铋化合物可任选地在本文使用。例如美国专利Nos.5,554,700；5,631,214；5,670,441；5,859,165；6,353,057和6,190,524中描述了这种类型的化合物。
任选的有机含铋化合物的实例包括乙酸铋、次乙酸铋、碳酸铋、水杨酸铋、次水杨酸铋、次碳酸铋、次柠檬酸铋、柠檬酸铋、苯甲酸铋、草酸铋、油酸铋、二烷基二硫代氨基甲酸铋、铋的羟基酸、有机硫铋化合物、铋与硫醇和/或羟基硫醇的反应产物、其混合物或组合等。
在一些实施方式中，无机含铋化合物可以与任选的多价金属催化剂组合使用，所述多价金属催化剂包括例如金属铋、锌、镉、铅、铁、钴、镍、钡、锶、铜、锆、锡、铬等。
当不期望或不需要不含锡的体系时，无机含铋的化合物可以与常规的有机锡化合物(例如DBTO、DOTO、DBTL等)一起使用。
在一个实施方式中，基于电沉积浴中固体的总重量，无机含铋化合物的存在量为约0.5-10重量％，更优选0.6-5重量％，最优选0.8-2重量％。如果无机含铋化合物与有机铋化合物或其它催化剂结合使用或组合使用，则无机含铋组合物以相应减少的量存在并用有机含铋化合物补充至组合量基于电沉积浴中固体的总重量为优选约0.5-10重量％，更优选0.6-5重量％，最优选0.8-0.2重量％。
在一个实施方式中，本文使用的无机含铋化合物还可以作为有效的腐蚀抑制剂起作用，其单独使用或与有机含铋化合物和/或本领域已知的其它腐蚀抑制剂组合使用。与本申请同日提交的题为“耐腐蚀组合物”(Corrosion Resistant Composition)的申请人的专利申请案号06-2468-0100中进一步描述了使用无机含铋化合物作为腐蚀抑制剂。
在一个实施方式中，相较于不使用无机含铋组合物制备的常规电沉积涂层，由本文所述的电沉积组合物和方法制成的固化涂层显示出比得上的耐腐蚀性，优选地更优的耐腐蚀性。
在各种实施方式中，电泳涂布组合物还可以包含一种或多种另外的组分，例如成膜剂、溶剂、聚结剂、表面活性剂、润湿剂、消泡剂、流变改性剂、填料、着色剂(例如颜料和染料)、杀生物剂、防霉剂或例如美国专利Nos.7,349,755和8,541,194以及申请人的美国临时申请No.62/164,870(于2015年5月21日提交)中所述的用于促进电沉积浴的透明度和健康的其它添加剂，以及上述组分的组合或混合物等。
合适的成膜剂的实例包括但不限于甲基苯酚和环氧丙烷的反应产物，例如可以以商标PARAPLEX(可从Dow商购)商购的那些。基于电沉积组合物中的固体的总重量，电泳涂布组合物中成膜剂的合适浓度优选为约0.1-3重量％，更优选约0.5-1重量％。
合适的表面活性剂的实例包括但不限于炔属醇，例如可以以商标″″表面活性剂(可从Air Products商购)商购的那些，及其组合。合适的润湿剂的实例包括但不限于烷基咪唑啉，例如可以以商标“GEIGY AMINE C”表面活性剂(CibaSpecialty Chemicals)商购的那些。基于电泳涂布组合物中固体的总重量，电泳涂布组合物中表面活性剂和润湿剂的合适浓度各自独立地为约0.1-2重量％，特别合适的浓度为约0.1-0.5重量％。
合适的消泡剂的实例包括但不限于上述表面活性剂和润湿剂、聚硅氧烷消泡剂(例如甲基烷基聚硅氧烷)及其组合。基于电泳涂布组合物中固体的总重量，电泳涂布组合物中消泡剂的合适浓度为约0.1-2重量％，特别合适的浓度为约0.1-0.5重量％。
合适的流变改性剂的实例包括触变材料。合适的触变材料包括聚酰胺、氧化聚乙烯及其组合。合适的市售触变材料的实例包括″″(King Industries，Inc.，Norwalk，Conn)系列的那些。基于电泳涂布组合物中固体的总重量，电泳涂布组合物中流变改性剂的合适浓度为约0.01-0.2重量％，特别合适的浓度为约0.01-0.1重量％。
合适的填料的实例包括二氧化硅、滑石、硅灰石、云母、三水合氧化铝、粘土、二氧化硅石英、碳酸钙、碳酸镁、碳酸钡、硫酸钙、硅酸铝、硫酸镁及其组合。合适的市售填料的实例包括商标为″″(Evonik Industries AG)的二氧化硅和″″(Elementis-Specialties，Inc.)系列的二氧化硅石英填料。
用于电泳涂布组合物中的合适着色剂的实例包括颜料，例如氧化铁、氧化铅、氧化锌、铬酸锶、铜铬、炭黑、煤粉、二氧化钛、硅酸铅、硫酸钡和及其组合。
电沉积组合物中包含合适量的颜料和/或填料以提供优选小于约0.5∶1，更优选0.5∶1至0.1∶1，甚至更优选0.2∶1至0.1∶1的颜料∶粘合剂比。
在一个实施方式中，本说明书提供了催化电沉积组合物固化的方法，所述方法包括以下步骤：提供可阳离子化的电沉积树脂组分、封闭异氰酸酯组分、脂族羧酸官能组分和包含至少一种无机含铋化合物的固化催化剂。在一方面，本文所述的方法用于通过电沉积方法涂布基材。
以前描述的适用于电泳涂布方法中的任何基材均可以在本文中使用。合适的实例包括但不限于冷轧钢、含有锆的冷轧钢、热浸镀锌钢、电镀锌钢、铝、锆等。通常并且优选地，在电沉积之前，向基材施加预处理。合适的预处理包括例如磷酸铁预处理、磷酸锌预处理、锆预处理等。预处理通常是用去离子水冲洗，和/或用铬酸盐封闭剂、非铬封闭剂或磷酸盐封闭剂等密封。
因此，在一个实施方式中，通过电沉积涂布基材的方法包括以下步骤：提供包含可阳离子化电沉积树脂组分和封闭多异氰酸酯交联剂组分的乳液。还提供了颜料糊，其优选包含任选的分散树脂、一种或多种颜料和至少一种无机含铋化合物。然后将乳液与颜料糊混合以形成电沉积组合物。用足够的去离子水稀释该组合物以形成起电沉积或电泳涂布浴的作用的水性分散体，基于电泳涂布组合物中固体的总重量，所述水性分散体的固体含量优选为5-35重量％，更优选约10-25重量％，甚至更优选为12-18重量％。
可以使基材经受电沉积以在基材上形成涂层。这可涉及将导电电极(阴极电沉积中的阳极)放置成与电沉积浴接触。将基材浸入浴中并与导电载体相连，从而允许基材起电极(阴极电沉积中的阴极)的作用。然后穿过水性分散体和基材诱导电位，从而使电泳涂布组合物沉积到基材上。
电泳涂布方法可以进行足够长的持续时间，以在基材上形成达到期望厚度的电泳涂布组合物的涂层，所述厚度优选为约5-50微米(约0.2-2密耳)，更优选约10-40微米(约0.5-1.5密耳)，最优选20-30微米(约0.8-1.2密耳)。涂层的厚度可以取决于多种因素，例如电泳涂布组合物的组成、水性分散体的固体浓度、基材的表面积和电势强度。通常且优选在10-65℃、更优选20-40℃的温度下，合适电势的实例为约50-500伏特、特别合适的电势为约100-350伏特。
在电泳涂布方法之后，可以冲洗经涂布的基材以期望地除去电泳涂布组合物的任何非结合部分。合适的冲洗流体的实例包括去离子水和/或从反应容器过滤的渗透物，其可以包括水、酸、溶剂、离子和低分子量树脂。然后可以加热经涂布的基材以固化涂层。在一个实施方式中，可以将经涂布的基材放置于保持在高温下的烘箱中足够的持续时间以固化涂层。温度优选足够高以从任选的异氰酸酯官能化合物中除去封闭剂，从而使环氧官能化合物与异氰酸酯官能化合物交联。用于固化电泳涂布组合物的合适温度的实例为约150℃至200℃，特别合适的温度优选为约175℃至190℃，更优选约160℃至180℃。在所述合适和特别合适的温度下基本固化涂层的合适持续时间的实例为约1-60分钟，特别优选的持续时间为约5-50分钟，更优选约10-45分钟，最优选约15-30分钟。
在一个实施方式中，电泳涂布方法可以以连续方式进行，其中在电泳涂布方法期间，基材可进入和离开反应容器。在这种实施方式中，可以将颜料糊部分、树脂部分和水性介质连续地或间歇地加入到反应容器中以保持期望的浓度比。基材的连续部分优选具有在反应容器中足够的停留时间以形成具有期望厚度的涂层。使用上述操作条件的连续电泳涂布方法的合适停留时间的实例为约1-300秒，优选10-250秒，更优选约60-180秒，最优选约90-120秒。此外，冲洗和固化步骤也可以在一条单独组装线中以连续方式进行，从而减少形成经涂布制品的时间。
在一个优选的方面，当在本文所述的方法中使用无机含铋化合物以形成电沉积涂层时，无机含铋化合物表现出最佳的催化效果，即其促进更快地固化或在更低温度下固化或二者。为了确定催化效果，根据如下文进一步描述的ASTM D5402-15的溶剂双向摩擦方法评估电沉积涂层的耐溶剂性。在至少20次、优选至少30次、更优选至少40次、最优选至少50次、最优选至少约100次双向摩擦之后，合适的涂层保持完整。
在一个实施方式中，使用本文所述方法制备的电沉积涂层在不利用其它腐蚀抑制剂的益处的情况下表现出最佳的耐腐蚀性，尽管如此也可以根据需要使用另外的腐蚀抑制剂。
在一个优选的方面，使用本文所述的方法制备的电沉积涂层表现出最佳的耐腐蚀性。根据如下文进一步描述的ASTM D1654-08的方法，将经涂布的试验板划线至金属并暴露于盐雾。合适的涂层显示出最小的漆料损失或优选小于约4mm，更优选小于约3mm，甚至更优选小于2mm，最优选小于1mm的划线蠕变。商业上可行的涂层通常具有小于3mm的划线蠕变。
所产生的经涂布制品期望地包含提供优异的腐蚀防护和最佳平滑度的涂层，同时也是环境友好的不含锡的体系。
实施例
通过以下实施例来阐释本发明。应该理解，具体的实例、材料、量和程序应该按照如本文所述的本发明的范围和精神广义地解释。除非另有声明，所有份和百分比均以重量计且所有分子量均是重均分子量。除非另外指出，使用的所有化合物均可商购自例如Sigma-Aldrich，St.Louis，Missouri。
试验方法
除非另有声明，在下面的实施例中使用如下试验方法。
耐溶剂性试验
测量涂层的“固化”或交联程度作为对溶剂(例如甲基乙基酮(MEK))的耐性。如ASTM D 5402-15(利用溶剂摩擦剂评估有机涂层的耐溶剂性的标准实践)中所述进行该试验。对于该试验而言，固化后1小时检测试验板上的电沉积膜，并在室温下检测板。膜的平均膜厚度为25μm，其涂覆在经磷酸铁预处理的(用DI冲洗)冷轧钢基材上。报告双向摩擦(即一次往复运动)的次数。
耐腐蚀性试验
如ASTM D1654-08(评估经受腐蚀性环境的涂漆或涂布样本的标准试验方法(Standard Practice for Assessing the Solvent Resistance of Organic CoatingsUsing Solvent Rubs))所述，通过测量暴露于腐蚀性环境之后的蠕变来检测由本文所述的组合物制备的固化涂层的耐腐蚀性。对于该试验而言，固化后1小时检测电沉积膜，并在室温下检测板。膜的平均膜厚度为25μm，其涂覆在各种不同的预处理金属基材的试验板上。将每块经涂布的板划线至金属并暴露于盐雾持续给定的时段。测量来自划线的漆料损失，并将结果表示为划线蠕变量(mm)。
实施例1.制备乳液
(a)制备扩链聚环氧化物
将以下成分加入配备有热源、搅拌器和回流装置的反应容器中：1439.4份EPON828(环氧当量为188的环氧树脂；Hexion Chemicals)、419.5份SYNFAC 8009(羟基当量为130的双酚A多元醇；Dow Chemical)。将装料在氮气层下加热至165℃。加入2.6份二甲基苄基胺，并将混合物保持在165℃持续1小时。加入另外5.2份二甲基苄胺，并将混合物保持在165℃直至环氧当量为820。加入1333份甲基异丁基酮(MIBK)溶剂。然后将混合物冷却至85℃，并加入185.9份二甲醇胺、100份MIBK和67.3份二乙基氨基丙胺。将混合物保持在120℃下持续1小时，加入93份MIBK。所得树脂溶液的不挥发物含量为62％。
(b)制备交联剂溶液
如下制备封闭多异氰酸酯交联树脂溶液：将862.0份丁基溶纤剂和172.2份三羟甲基丙烷加入到如实施例1所配备的反应容器中。将混合物加热至60℃，并在氮气层下将1419份LUPRANATE 266(低粘度异氰酸酯；BASF)小心地加入到混合物中，同时保持反应混合物低于90℃。然后加入13.2份丁基溶纤剂并将混合物保持在96℃下持续2小时直至基本上所有的游离异氰酸酯均被消耗。然后加入1038.4份MIBK。所得混合物的不挥发物含量为70.0％。
(c)制备乳液
将1089.7份来自实施例1(a)的扩链聚环氧化物与642.8份来自实施例1(b)的交联剂溶液、3.6份SURFYNOL 104(表面活性剂；Air Products)、DOWANOL PPh溶剂(二醇醚；DowChemical)和64.8份88％的乳酸溶液一起加入不锈钢烧杯中，并利用高速空气混合器充分混合。然后在搅拌条件下加入2106份去离子水。将混合物混合直到大部分有机酮蒸发。使用去离子水将所得乳液的不挥发物含量调节至36％。
实施例2.制备颜料糊
(a)制备颜料分散树脂
如下制备季铵化剂：在室温下，在合适的反应容器中，向通过将80份MIBK与696.8份TDI和520份2-乙基己醇混合制得的半加帽(capped)甲苯二异氰酸酯(TDI)中加入356.6份二甲基乙醇胺。混合物放热，在80℃下搅拌1小时。然后将400.9份乳酸加入容器中，接着加入156份丁基溶纤剂。在65℃下搅拌反应混合物约1小时以形成期望的季铵化剂。
如下制备颜料研磨载剂：在氮气气氛下，将491份EPON 829(双酚A的二缩水甘油醚；Hexion)和双酚加入合适的反应混合物中。使反应混合物在150℃至160℃下放热约1小时，然后冷却至120℃，然后加入上文制备的2-乙基己醇半加帽TDI。将反应混合物的温度保持在110℃至120℃持续1小时，然后加入丁基溶纤剂。然后将反应混合物冷却至85℃，均化并加入水，随后加入上文制备的季铵化剂。将反应混合物的温度保持在80℃至85℃直到酸值为1.0。所得产物的非挥发物含量为58％。
(b)制备颜料糊#1
将420.65份非挥发物含量为53.2％的来自实施例2(a)的颜料分散树脂与500.0份去离子水、5.54份SURFYNOL 104A(Air Products)、119.8份RAVEN 850炭黑粉末、178.92份ASP(BASF)、170份硅酸铝和110份铝酸铋水合物一起加入合适的容器中。将内容物混合直至均匀，然后在水平介质研磨机中分散直至Hegman读数为7。所得材料的非挥发物含量为47.0％。
(c)制备颜料糊#2
将420.65份非挥发物含量为53.2％的来自实施例2(a)的颜料分散树脂与558.8份去离子水、5.54份SURFYNOL 104A(Air Products)、119.8份RAVEN 850炭黑粉末、178.92份ASP(BASF)、170份硅酸铝、27份铝酸铋水合物、37份柠檬酸铋和203份去离子水一起加入合适的容器中。将内容物混合直至均匀，然后在水平介质研磨机中分散直至Hegman读数为7。所得材料的非挥发物含量为36.7％。
实施例3.电沉积浴和涂料#1
如下制备电泳涂布或电沉积浴：在4.0L烧杯中，利用低速搅拌，将900份来自实施例1的乳液与3340.8份实施例2的颜料糊#1以及2759.2份去离子水混合。将该浴保持在32℃，并在200伏下阴极电泳涂布如表2所示的各种基材的试验板两分钟。然后在各种不同的温度下固化经涂布的板20分钟以提供0.65密耳(约16μm)的成膜。
实施例4.电沉积浴和涂料#2
如下制备电泳涂布或电沉积浴：在4.0L烧杯中，利用低速搅拌，将900份来自实施例1的乳液与390份实施例2的颜料糊#2以及2710份去离子水混合。将该浴保持在32℃，并在200伏下阴极电泳涂布如表3所示的各种基材的试验板两分钟。然后在各种不同的温度下固化经涂布的板20分钟以提供0.65密耳(约16μm)的成膜。
实施例5.耐溶剂性
来自实施例3和4的经涂布板展示出超常的平滑度。为了检测固化性能，使用MEK双向摩擦方法以及涂布有使用标准DBTO催化剂的组合物的对照试验板检测经涂布板的耐溶剂性。结果在表2中显示为漆料损失所需的MEK双向摩擦的次数。涂布有实施例3和4的涂料的板显示出没有光泽损失或漆料损失。此外，固化膜在于MEK中浸泡1分钟后不软化。
表1.固化性能
*严重损毁
**一定程度的损毁
实施例6.耐腐蚀性
根据上述方法，将来自实施例3和4的经涂布板划线并暴露于盐750小时以评价耐腐蚀性。盐雾暴露750小时之后，在180℃下烘烤划线的板20分钟。然后刮擦板，并测量划线蠕变。表2中显示了至少五块板的平均划线蠕变。
表2.平均划线蠕变
本文中引用的所有专利、专利申请和出版物以及电子可得材料的全部公开内容通过引用并入本文。给出上述详细说明和实施例仅仅是为了清楚理解。不应由其理解为不必要的限制。本发明并不局限于所表明和所描述的精确细节，对于本领域技术人员来说明显的变化包含在权利要求书所限定的本发明的范围内。在一些实施方式中，在无任何未具体公开的元素的情况下，可以适当地实施本文中以说明方式公开的本发明。
Claims (21)
1.涂料组合物，其包含：
含有催化有效量的无机含铋化合物的可电沉积组合物。
2.用于电沉积的组合物，其包含：
电沉积树脂组分；
任选的交联组分；
任选的酸组分；和
至少金属氧阴离子的无机铋盐。
3.方法，其包括：
将包含至少一种可交联官能团的电沉积树脂组分与以下物质组合：
封闭异氰酸酯组分；
脂族羧酸组分；和
至少金属氧阴离子的无机铋盐。
4.使用固化催化剂的方法，其包括：
提供至少包含催化有效量的无机含铋化合物作为固化催化剂的组合物；和
向使用者提供将所述包含固化催化剂的组合物加入电沉积浴中的指示。
5.电沉积方法，其包括：
提供包含可阳离子化电沉积树脂组分和封闭多异氰酸酯交联剂组分的乳液；
提供包含分散树脂、颜料和金属氧阴离子的无机铋盐的颜料糊；
将所述电沉积树脂和所述颜料糊与水混合以形成电沉积浴；和
施加电压以阴极电泳涂布基材。
6.根据上述权利要求中任一项所述的组合物或方法，其中所述无机含铋化合物是在约4-6的pH和约37℃的温度下基本上不溶于水的化合物。
7.根据上述权利要求中任一项所述的组合物或方法，其中所述无机含铋化合物选自硅酸铋、硅铝酸铋镁、铝酸铋、硼酸铋、锰酸铋、磷酸铋、及其混合物或组合。
8.根据权利要求1-4中任一项所述的组合物或方法，其中所述无机含铋化合物是金属氧阴离子的铋盐。
9.根据上述权利要求中任一项所述的组合物或方法，其中所述无机含铋化合物是铝酸铋。
10.根据上述权利要求中任一项所述的组合物或方法，其中所述组合物包括无机含铋化合物和有机含铋化合物的组合。
11.根据前述权利要求中任一项所述的组合物或方法，其中所述组合物包含无机含铋化合物和有机含铋化合物的组合，所述有机含铋化合物选自乙酸铋、次乙酸铋、碳酸铋、水杨酸铋、次水杨酸铋、次碳酸铋、次柠檬酸铋、柠檬酸铋、苯甲酸铋、草酸铋、油酸铋、二烷基二硫代氨基甲酸铋、铋的羟基酸、有机硫铋化合物、铋与硫醇和/或羟基硫醇的反应产物、其混合物或组合。
12.根据前述权利要求中任一项所述的组合物或方法，其中所述组合物包含无机含铋化合物和柠檬酸铋的组合。
13.根据前述权利要求中任一项所述的组合物或方法，其中所述组合物包含铝酸铋和柠檬酸铋的组合。
14.权利要求1所述的组合物，其还包含：
约40-95重量％的电沉积树脂组分；
约10-60重量％的封闭多异氰酸酯组分；
约1-10重量％的脂族羧酸组分；和
约0.5-10重量％的无机含铋化合物。
15.通过上述权利要求中任一项所述的方法形成的经涂布制品。
16.通过电沉积上述权利要求中任一项所述的组合物的膜来制备经涂布制品的方法。
17.根据前述权利要求中任一项所述的方法，其中所述膜具有10-25μm的平均厚度。
18.阳离子电沉积浴，其包含上述权利要求中任一项所述的组合物。
19.根据上述权利要求中任一项所述的组合物、制品或方法，其中由所述组合物形成的涂层具有耐腐蚀性。
20.根据上述权利要求中任一项所述的组合物、制品或方法，其中根据ASTM D1654-08，由所述组合物形成的涂层展示出小于3mm的划线蠕变，其中将所述涂层涂覆在预处理的冷轧钢基材上。
21.根据上述权利要求中任一项所述的组合物、制品或方法，其中根据ASTM D5402-15，由所述组合物形成的涂层展示出至少30次双向摩擦的耐溶剂性。
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| US201562114228P | 2015-02-10 | 2015-02-10 | |
| US62/114,228 | 2015-02-10 | ||
| PCT/US2016/017323 WO2016130656A1 (en) | 2015-02-10 | 2016-02-10 | Novel electrodeposition system |
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| EP (1) | EP3256533B1 (zh) |
| JP (1) | JP6744320B2 (zh) |
| KR (1) | KR102584869B1 (zh) |
| CN (1) | CN107406696A (zh) |
| AU (1) | AU2016219368B2 (zh) |
| BR (1) | BR112017015460B1 (zh) |
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| MX (1) | MX2017009782A (zh) |
| MY (1) | MY184093A (zh) |
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| WO2016130656A1 (en) | 2015-02-10 | 2016-08-18 | Valspar Sourcing, Inc. | Novel electrodeposition system |
| WO2016187618A1 (en) * | 2015-05-21 | 2016-11-24 | Valspar Sourcing, Inc. | Antimicrobial agent for powder coating compositions |
| EP3414290A4 (en) * | 2016-02-10 | 2019-12-18 | Swimc LLC | ANTI-CORROSION COMPOSITION |
| EP3534712B1 (en) | 2016-11-03 | 2022-12-28 | Swimc Llc | Antimicrobial agent for coatings and finishes |
| ES2967234T3 (es) * | 2018-08-24 | 2024-04-29 | Covestro Intellectual Property Gmbh & Co Kg | Composición de poliuretano, procedimiento de preparación y aplicación de la misma |
| CN109482213B (zh) * | 2018-12-29 | 2021-03-09 | 陕西师范大学 | 一种Bi/(BiO)2CO3纳米花球状光催化剂的制备方法 |
| US20210238439A1 (en) * | 2019-12-30 | 2021-08-05 | Axalta Coating Systems Ip Co., Llc | Low density electrocoat composition with improved throwing power |
| US11466175B2 (en) * | 2019-12-30 | 2022-10-11 | Ppg Industries Ohio, Inc. | Silicone-based electrodepositable coating composition |
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Also Published As
| Publication number | Publication date |
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| KR102584869B1 (ko) | 2023-10-06 |
| US20200231823A1 (en) | 2020-07-23 |
| BR112017015460B1 (pt) | 2022-08-02 |
| RU2017123534A3 (zh) | 2019-03-12 |
| AU2016219368B2 (en) | 2020-05-07 |
| US10655023B2 (en) | 2020-05-19 |
| MY184093A (en) | 2021-03-17 |
| EP3256533A1 (en) | 2017-12-20 |
| WO2016130656A1 (en) | 2016-08-18 |
| EP3256533B1 (en) | 2024-04-24 |
| KR20170120570A (ko) | 2017-10-31 |
| CA2973766A1 (en) | 2016-08-18 |
| RU2684081C2 (ru) | 2019-04-03 |
| RU2017123534A (ru) | 2019-03-12 |
| CA2973766C (en) | 2024-02-13 |
| BR112017015460A2 (pt) | 2018-01-23 |
| MX2017009782A (es) | 2017-10-27 |
| JP6744320B2 (ja) | 2020-08-19 |
| CL2017002046A1 (es) | 2018-02-16 |
| US20170335120A1 (en) | 2017-11-23 |
| US11466164B2 (en) | 2022-10-11 |
| AU2016219368A1 (en) | 2017-07-27 |
| JP2018510924A (ja) | 2018-04-19 |
| EP3256533A4 (en) | 2018-09-26 |
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